5-溴-4-(4-甲氧基苯基)嘧啶 | 941294-41-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-4-(4-甲氧基苯基)嘧啶
• 英文名称: 5-bromo-4-(4-methoxyphenyl)pyrimidine
• CAS: 941294-41-3
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: PMJDLHCYVVWSTG-UHFFFAOYSA-N

物化性质

• 沸点：
  369.0±32.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933599090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Bromo-4-(4-methoxyphenyl)pyrimidine
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromo-4-(4-methoxyphenyl)pyrimidine
CAS number: 941294-41-3

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H9BrN2O
Molecular weight: 265.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-溴-4-(4-甲氧基苯基)嘧啶 在 2-溴吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.42h， 生成
  参考文献：
  名称：

  通过骨骼编辑实现氮杂芳烃的 14N 到 15N 同位素交换

  摘要：

  氮杂芳烃的选择性改性使新化学工具的开发成为可能，并加速了药物发现。虽然专注于扩展或收缩杂芳烃骨架结构的方法正在出现，但直接交换单核原子的方法仍然有限。在这里，我们提出了一种对几种芳香族氮杂环进行 14N → 15N 同位素交换的方法。这种氮同位素嬗变是通过氮原子的三飞化激活杂芳烃底物而发生的，然后是由 15个 N-天冬氨酸介导的开环/闭环序列，以实现氮原子的同位素交换。这种转化成功的关键是形成可分离的 15N-琥珀酰中间体，该中间体经过消除以得到同位素标记的杂环。这些转化发生在温和的条件下，化学和同位素产量高。

  DOI：

  10.1021/jacs.3c11515
• 作为产物：
  描述：

  苯甲醚 在 甲烷磺酸 、 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 为溶剂， 反应 2.5h， 生成 5-溴-4-(4-甲氧基苯基)嘧啶
  参考文献：
  名称：

  芳烃与 5-溴嘧啶在生成 4-芳基-5-炔基嘧啶的过程中的亲电烷基化

  摘要：

  描述了一种用于制备具有重要药用价值的 4-aryl-5-alkynylpyrimidines 的新合成方案。特色方法涉及一系列化学和区域选择性布朗斯台德酸催化的芳烃与 5-溴嘧啶的亲电烷基化，然后对形成的二氢嘧啶环进行氧化再芳构化。最后，钯催化的 Sonogashira 交叉偶联反应提供了一种最终策略。

  DOI：

  10.1039/d0ra01335h

文献信息

• Direct Arylation of N-Heteroarenes with Aryldiazonium Salts by Photoredox Catalysis in Water
  作者：Dong Xue、Zhi-Hui Jia、Cong-Jun Zhao、Yan-Yan Zhang、Chao Wang、Jianliang Xiao

  DOI：10.1002/chem.201304120

  日期：2014.3.3

  solvent, an array of xanthenes, thiazole, pyrazine, and pyridazine are compatible with this new arylation approach. The broad substrate scope, mild reaction conditions, and use of water as reaction solvent make this procedure a practical and environmentally friendly method for the synthesis of compounds containing aryl‐heteroaryl motifs.

  已经开发出一种高效的可见光促进的N-杂芳烃与芳基重氮盐在水中的“自由基型”偶联。在室温下将反应继续进行的[Ru（联吡啶）3 ]氯2 ⋅ 6 H 2O作为光敏剂，商用灯泡作为光源。在这些反应条件下，吡啶和各种取代的吡啶是有效的底物，仅形成具有不同区域选择性的单取代产物。使用甲酸水溶液作为溶剂，一系列的黄嘌呤，噻唑，吡嗪和哒嗪与这种新的芳基化方法兼容。广泛的底物范围，温和的反应条件以及使用水作为反应溶剂，使得该程序成为合成具有芳基-杂芳基基序的化合物的实用且环境友好的方法。
• Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
  作者：Stanislav S. Shcherbakov、Artyom Yu. Magometov、Viktoriia Yu. Shcherbakova、Alexander V. Aksenov、Dmitriy A. Domenyuk、Vladimir A. Zelensky、Michael Rubin

  DOI：10.1039/d0ra01335h

  日期：——

  4-aryl-5-alkynylpyrimidines is described. The featured approach involves a sequence of chemo- and regioselective Brønsted acid-catalyzed electrophilic alkylation of arenes with 5-bromopyrimidine, followed by oxidative re-aromatization of the formed dihydropyrimidine ring. Finally, palladium-catalyzed Sonogashira cross-coupling reaction provided an end-game strategy.

  描述了一种用于制备具有重要药用价值的 4-aryl-5-alkynylpyrimidines 的新合成方案。特色方法涉及一系列化学和区域选择性布朗斯台德酸催化的芳烃与 5-溴嘧啶的亲电烷基化，然后对形成的二氢嘧啶环进行氧化再芳构化。最后，钯催化的 Sonogashira 交叉偶联反应提供了一种最终策略。
• Investigation of cationic transformations involving 5-ethynyl-4-arylpyrimidines
  作者：Stanislav V. Shcherbakov、Artyom Yu Magometov、Maksim V. Vendin、Viktoria Yu Shcherbakova、Nicolai A. Aksenov、Alexander V. Aksenov、Osama Naji、Michael Rubin

  DOI：10.1016/j.tet.2022.132796

  日期：2022.6

  acid-catalyzed electrophilic alkylation of phenols with 5-bromopyrimidine, followed by oxidation and palladium-catalyzed Sonogashira cross-coupling reaction. Reactions of these compounds in the presence of trifluoromethanesulfonic acid were investigated. It was discovered these reactions take a different route for precursors with a different position of phenol group in an arene substituent.

  开发了一种创新的 5-乙炔基-4-芳基嘧啶合成方法，包括用 5-溴嘧啶对酚进行酸催化的亲电烷基化，然后进行氧化和钯催化的 Sonogashira 交叉偶联反应。研究了这些化合物在三氟甲磺酸存在下的反应。发现对于芳烃取代基中苯酚基位置不同的前体，这些反应采用不同的途径。
• ¹⁴N to ¹⁵N Isotopic Exchange of Nitrogen Heteroaromatics through Skeletal Editing
  作者：G. Logan Bartholomew、Samantha L. Kraus、Lucas J. Karas、Filippo Carpaneto、Raffeal Bennett、Matthew S. Sigman、Charles S. Yeung、Richmond Sarpong

  DOI：10.1021/jacs.3c11515

  日期：2024.2.7

  selective modification of nitrogen heteroaromatics enables the development of new chemical tools and accelerates drug discovery. While methods that focus on expanding or contracting the skeletal structures of heteroaromatics are emerging, methods for the direct exchange of single core atoms remain limited. Here, we present a method for 14N → 15N isotopic exchange for several aromatic nitrogen heterocycles

  氮杂芳烃的选择性改性使新化学工具的开发成为可能，并加速了药物发现。虽然专注于扩展或收缩杂芳烃骨架结构的方法正在出现，但直接交换单核原子的方法仍然有限。在这里，我们提出了一种对几种芳香族氮杂环进行 14N → 15N 同位素交换的方法。这种氮同位素嬗变是通过氮原子的三飞化激活杂芳烃底物而发生的，然后是由 15个 N-天冬氨酸介导的开环/闭环序列，以实现氮原子的同位素交换。这种转化成功的关键是形成可分离的 15N-琥珀酰中间体，该中间体经过消除以得到同位素标记的杂环。这些转化发生在温和的条件下，化学和同位素产量高。